76685-16-0

Upstream product

• 63696-99-1 (S)-ethyl 2-(methylsulfonyloxy)propanoate 
• 108-98-5 thiophenol 
• 84028-89-7 ethyl (R)-2-trifluoromethylsulfonyloxypropanoate 
• 13133-62-5 thiophenolate 
• 535-11-5 Ethyl 2-bromopropionate 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 
• 6111-99-5 ethyl diazoalaninate 

Downstream Products

• 146300-52-9 (R)-α-(phenylthio)propanoic acid 
• 125660-37-9 (R)-2-Phenylsulfanyl-propionaldehyde 
• 125713-06-6 (4S,5R,8R,9R)-5-Methoxymethoxy-2-phenyl-8-((R)-1-phenylsulfanyl-ethyl)-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione 
• 125660-43-7 (4R,5S,8S,9S)-5-Methoxymethoxy-2-phenyl-8-((R)-1-phenylsulfanyl-ethyl)-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione 
• 125713-04-4 (4aS,5R,8S,8aR)-5-Methoxymethoxy-8-((R)-1-phenylsulfanyl-ethyl)-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 
• 125660-41-5 (4aR,5S,8R,8aS)-5-Methoxymethoxy-8-((R)-1-phenylsulfanyl-ethyl)-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 
• 125660-39-1 4-Methoxymethoxy-2-phenyl-7-((R)-1-phenylsulfanyl-ethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione 
• 125660-36-8 ((2E,4E)-(R)-5-Methoxymethoxy-1-methyl-penta-2,4-dienylsulfanyl)-benzene 
• 146608-23-3 (R)-2-<(R)-Phenylsulfinyl>propionsaeure 
• 146608-25-5 (R)-2-<(S)-Phenylsulfinyl>propionsaeure Dicyclohexylammoniumsalz 
• 146300-55-2 2-Phenylselenyl-2-<(S)-phenylsulfinyl>propionsaeuremethylester 
• 58793-82-1 2-<(R)-Phenylsulfinyl>propionsaeuremethylester 
• 146300-57-4 2-<(S)-Phenylsulfinyl>acrylsaeuremethylester 

Relevant academic research and scientific papers

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS

Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

CsF in organic synthesis. Inversion of secondary mesylates and tosylates

Clean inversion of secondary mesylates and tosylates is effected by CsF in DMF. A variety of oxygen-, sulfur-, nitrogen-, and carbon-nucleophiles are employable. The reaction conditions have been optimized. The use of CsF in DMF is crucial and the reaction proceeds on the surface of solid CsF. It is suggested that hydrogen bonding between CsF and an active hydrogen of nucleophiles is responsible for the smooth reaction. Cesium carbonate fails to give rise to high specificity of inversion indicative of superiority of CsF.

Preparation of enantiomerically pure sulfoxides from lactic acid and 3-hydroxybutyric acid. Isopropenyl tolyl sulfoxide and 2-(phenylsulfinyl)acrylate

The EPC-synthesis of sulfoxides from readily available starting materials ('chiral pool') is demonstrated for the first time. Cyclic and open-chain thioethers derived from lactic and 3-hydroxybutyric acid are oxidized to sulfoxides, and the resulting prod

Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization

The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.

PHASE TRANSFER CATALYSIS USING CHIRAL CATALYSTS. V. ASYMMETRIC NUCLEOPHILIC SUBSTITUTIONS WITH C, O, N AND S-ANIONS

Several asymmetric nucleophilic substitutions with C, N, O and S-anions have been performed under PTC conditions using chiral quaternary ammonium salts as PT catalysts.